If my memory serves correctly, it was something along the lines of this:
->

Boy hurtles into the world, crashing and losing his memories as a result.

He's a pirate? Somebody on a floating city takes him in, and he serves as an assistant.

He goes north to this forest that's incredibly dangerous at night and goes to a slave market and fights in a gladiator ring.

He escapes and falls down this hole into the people-group's disposal system, which is like a giant everything-eating organism (excuse my phrasing, please)

The book had illustrations. Black-and-white ones, and was in a series. This may have been the third or fourth book. I think the binding was tan, but I'm not too sure.

Miscellaneous details: There's a floating/or on a mountain academy-city; man-eating snails; giant, man-eating forests at night; a generally dark tone; swamps?; most likely published in the late 90's ('98 and up) and early 2000's, because I remember reading this in 2005 or 2006.

1 Answer
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The series started centered around Twig, a young orphan who was raised in the Deep Woods. He is sent off to find his own kind and has all sorts of adventures underway, meeting the strangest creatures.

Twig is main character in a few books, one features his father as main character and other books have different protagonists, only loosely connected with Twig. There is also a creature guide.

I have read only five books, and I was charmed by the diversity and non-D&D-ness of the creatures. It is a series of children's book though, so cynical adults will probably think them childish. (be warned! But for kids a great read, with proper adventure, fun and drama).